IP Library › Granted Patent US 9,180,115
Granted Patent B2
US 9,180,115 · App. 14/220,381 · Granted Nov 10, 2015

Cyclohexylamines

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Quick Facts
Patent No.
US 9,180,115
App. No.
14/220,381
Granted
Nov 10, 2015
Kind
B2
Abstract

The present application provides novel compounds and methods for preparing and using these compounds. These compounds are useful in treating pain, itch, overactive bladder and/or interstitial cystitis in patients by administering one or more of the compounds to a patient. The methods include administering a compound of formula (I) and a TRPV1 receptor activator. In one embodiment, the TRPV1 receptor activator is lidocaine.

Claims (428)

1. A method of treating pain in a patient, comprising administering to said patient a therapeutically effective amount of a compound selected from the group consisting of:

N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide.

N-[2-(Benzoyloxy)propyl]-N,N-diethylcyclohexanaminium chloride;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethoxybenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((3-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Fluoro-2-(trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-(Trifluoromethyl)benzoyl)oxy)propyl]l-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-nitrobenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3,5-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)—N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)—N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)—N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)—N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]tetrahydro-2H-pyran-4-aminium iodide;

N-[2-((2,3-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((Cyclohexanecarbonyl)oxy)propyl]-N,N-diethylcyclohexanaminium iodide;

N-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-3-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((1-methyl-1H-pyrrole-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((Benzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-methylthiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N,4-Trimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4,6-Trimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide;

(R)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide;

1-Cyclohexyl-1-[2-((2-isopropylbenzoyl)oxy)propyl]pyrrolidin-1-ium bromide;

1-Cyclohexyl-1-[2-((2-isopropylbenzoyl)oxy)propyl]piperidin-1-ium bromide;

1-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-1-cyclohexylpyrrolidin-1-ium bromide;

1-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-1-cyclohexylpiperidin-1-ium bromide;

1-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-1-cyclohexylpyrrolidin-1-ium bromide; and

1-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-1-cyclohexylpiperidin-1-ium bromide.

2. The method of claim 1 , wherein said administration is topical.

3. A method of treating pain in a patient, comprising administering to said patient a therapeutically effective amount of a compound selected from the group consisting of:

(i) N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-(Benzoyloxy)propyl]-N,N-diethylcyclohexanaminium chloride;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethoxybenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((3-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Fluoro-2-(trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-(Trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-nitrobenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3,5-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)—N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)—N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)—N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)—N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]tetrahydro-2H-pyran-4-aminium iodide;

N-[2-((2,3-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((Cyclohexanecarbonyl)oxy)propyl]-N,N-diethylcyclohexanaminium iodide;

N-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-3-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((1-methyl-1H-pyrrole-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((Benzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-methylthiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N,4-Trimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4,6-Trimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide;

(R)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide;

1-Cyclohexyl-1-[2-((2-isopropylbenzoyl)oxy)propyl]pyrrolidin-1-ium bromide;

1-Cyclohexyl-1-[2-((2-isopropylbenzoyl)oxy)propyl]piperidin-1-ium bromide;

1-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-1-cyclohexylpyrrolidin-1-ium bromide;

1-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-1-cyclohexylpiperidin-1-ium bromide;

1-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-1-cyclohexylpyrrolidin-1-ium bromide; and

1-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-1-cyclohexylpiperidin-1-ium bromide; and

(ii) a TRPV1 receptor activator.

4. The method of claim 3 , wherein said TRPV1 receptor activator is selected from the group consisting of capsaicin, dihydrocapsaicin, nordihydrocapsaicin, lidocaine, articaine, procaine, tetracaine, mepivicaine, bupivicaine, eugenol, camphor, clotrimazole, N-arachidonoylvanillamine, anandamide, 2-aminoethoxydiphenyl borate, AM404, resiniferatoxin, phorbol 12-phenylacetate 13-acetate 20-homovanillate, olvanil, N-oleoyldopamine, N-arachidonyldopamine, 6′-iodoresiniferatoxin, a C 18 N-acylethanolamine, a lipoxygenase derivative, nonivamide, a fatty acyl amide of a tetrahydroisoquinoline inhibitor cysteine knot peptide, N-[2-(3,4-dimethylbenzyl)-3-(pivaloyloxy)propyl]-2-[4-(2-aminoethoxy)-3-methoxyphenyl]acetamide, N-[2-(3,4-dimethylbenzyl)-3-(pivaloyloxy)propyl]-N′-(4-hydroxy-3-methoxybenzyl)thiourea, hydroxy-α-sanshool, 2-aminoethoxydiphenyl borate, 10-shogaol, oleylgingerol, oleylshogaol, N-(4-tert-butylbenzyl)-N′-(4-hydroxy-3-methoxybenzyl)thiourea, aprindine, benzocaine, butacaine, cocaine, dibucaine, encainide, mexiletine, oxetacaine, prilocaine, proparacaine, procainamide, n-acetylprocainamide, chloroprocaine, dyclonine, etidocaine, levobupivacaine, ropivacaine, cyclomethycaine, dimethocaine, propoxycaine, trimecaine, and sympocaine.

5. The method of claim 3 or 4 , wherein said administration is topical.

6. The method of claim 3 , wherein said TRPV1 receptor activator of (ii) is co-administered with said compound of (i).

7. The method of claim 3 , wherein said TRPV1 receptor activator of (ii) is administered prior to said compound of (i).

8. A method of treating itch in a patient, comprising administering to said patient a therapeutically effective amount of a compound selected from the group consisting of:

N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-(Benzoyloxy)propyl]-N,N-diethylcyclohexanaminium chloride;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethoxybenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((3-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Fluoro-2-(trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-(Trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-nitrobenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3,5-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)—N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)—N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)—N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)—N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]tetrahydro-2H-pyran-4-aminium iodide;

N-[2-((2,3-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((Cyclohexanecarbonyl)oxy)propyl]-N,N-diethylcyclohexanaminium iodide;

N-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-3-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((1-methyl-1H-pyrrole-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((Benzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-methylthiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N,4-Trimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4,6-Trimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide;

(R)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide;

1-Cyclohexyl-1-[2-((2-isopropylbenzoyl)oxy)propyl]pyrrolidin-1-ium bromide;

1-Cyclohexyl-1-[2-((2-isopropylbenzoyl)oxy)propyl]piperidin-1-ium bromide;

1-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-1-cyclohexylpyrrolidin-1-ium bromide;

1-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-1-cyclohexylpiperidin-1-ium bromide;

1-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-1-cyclohexylpyrrolidin-1-ium bromide; and

1-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-1-cyclohexylpiperidin-1-ium bromide.

9. The method of claim 8 , wherein said administration is topical.

10. A method of treating itch in a patient, comprising administering to said patient a therapeutically effective amount of a compound selected from the group consisting of:

(i) N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-(Benzoyloxy)propyl]-N,N-diethylcyclohexanaminium chloride;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethoxybenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((3-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Fluoro-2-(trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-(Trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-nitrobenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3,5-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)—N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)—N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)—N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)—N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]tetrahydro-2H-pyran-4-aminium iodide;

N-[2-((2,3-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((Cyclohexanecarbonyl)oxy)propyl]-N,N-diethylcyclohexanaminium iodide;

N-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-3-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((1-methyl-1H-pyrrole-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((Benzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-methylthiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N,4-Trimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4,6-Trimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide;

(R)—N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide;

1-Cyclohexyl-1-[2-((2-isopropylbenzoyl)oxy)propyl]pyrrolidin-1-ium bromide;

1-Cyclohexyl-1-[2-((2-isopropylbenzoyl)oxy)propyl]piperidin-1-ium bromide;

1-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-1-cyclohexylpyrrolidin-1-ium bromide;

1-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-1-cyclohexylpiperidin-1-ium bromide;

1-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-1-cyclohexylpyrrolidin-1-ium bromide; and

1-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-1-cyclohexylpiperidin-1-ium bromide; and

(ii) a TRPV1 receptor activator.

11. The method of claim 10 , wherein said TRPV1 receptor activator is selected from the group consisting of capsaicin, dihydrocapsaicin, nordihydrocapsaicin, lidocaine, articaine, procaine, tetracaine, mepivicaine, bupivicaine, eugenol, camphor, clotrimazole, N-arachidonoylvanillamine, anandamide, 2-aminoethoxydiphenyl borate, AM404, resiniferatoxin, phorbol 12-phenylacetate 13-acetate 20-homovanillate, olvanil, N-oleoyldopamine, N-arachidonyldopamine, 6′-iodoresiniferatoxin, a C 18 N-acylethanolamine, a lipoxygenase derivative, nonivamide, a fatty acyl amide of a tetrahydroisoquinoline inhibitor cysteine knot peptide, N-[2-(3,4-dimethylbenzyl)-3-(pivaloyloxy)propyl]-2-[4-(2-aminoethoxy)-3-methoxyphenyl]acetamide, N-[2-(3,4-dimethylbenzyl)-3-(pivaloyloxy)propyl]-N′-(4-hydroxy-3-methoxybenzyl)thiourea, hydroxy-α-sanshool, 2-aminoethoxydiphenyl borate, 10-shogaol, oleylgingerol, oleylshogaol, N-(4-tert-butylbenzyl)-N′-(4-hydroxy-3-methoxybenzyl)thiourea, aprindine, benzocaine, butacaine, cocaine, dibucaine, encainide, mexiletine, oxetacaine, prilocaine, proparacaine, procainamide, n-acetylprocainamide, chloroprocaine, dyclonine, etidocaine, levobupivacaine, ropivacaine, cyclomethycaine, dimethocaine, propoxycaine, trimecaine, and sympocaine.

12. The method of claim 10 or 11 , wherein said administration is topical.

13. The method of claim 10 , wherein said TRPV1 receptor activator of (ii) is co-administered with said compound of (i).

14. The method of claim 10 , wherein said TRPV1 receptor activator of (ii) is administered prior to said compound of (i).

15. The method of claim 1 , wherein the compound is selected from the group consisting of:

N-[2-((2,6-Dimethylbenzoy)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-(Benzoyloxy)propyl]-N,N-diethylcyclohexanaminium chloride;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethoxybenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide; and

N-[2-((4-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide.

N-[2-((3-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Fluoro-2-(trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-(Trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-nitrobenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3,5-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)-N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)-N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]tetrahydro-2H-pyran-4-aminium iodide;

N-[2-((2,3-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((Cyclohexanecarbonyl)oxy)propyl]-N,N-diethylcyclohexanaminium iodide;

N-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-3-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((l-methyl-1H-pyrrole-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((Benzo[b]thiophene-2-carbonyl)oxy)propyl] -N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-(3-methylthiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N, 4 -Trimethyl-N-[2-(2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4,6-Trimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide; and

(R)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide.

16. The method of claim 3 , wherein the compound is selected from the group consisting of:

N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-(Benzoyloxy)propyl]-N,N-diethylcyclohexanaminium chloride;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethoxybenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((3-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-(4-Fluoro-2-(trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-(Trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-nitrobenzoyl(oxy)propyl]cyclohexanaminium iodide;

N-[2-(3,5-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)-N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)-N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]tetrahydro-2H-pyran-4-aminium iodide;

N-[2-((2,3-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((Cyclohexanecarbonyl)oxy)propyl]-N,N-diethylcyclohexanaminium iodide;

N-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-3-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((1-methyl-1H-pyrrole-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((Benzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-methylthiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N,4-Trimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4,6-Trimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide; and

(R)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide.

17. The method of claim 8 , wherein the compound is selected from the group consisting of:

N-[2-(2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-(Benzoyloxy)propyl]-N,N-diethylcyclohexanaminium chloride;

N,N-Dimethyl-N-[2-(2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethoxybenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-(2-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-(3-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Fluoro-2-(trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-(Trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-nitrobenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3,5-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)-N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)-N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]tetrahydro-2H-pyran-4-aminium iodide;

N-[2-((2,3-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((Cyclohexanecarbonyl)oxy)propyl]-N,N-diethylcyclohexanaminium iodide;

N-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-3-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((1-methyl-1H-pyrrole-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((Benzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-methylthiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N,4-Trimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4,6-Trimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide; and

(R)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide.

18. The method of claim 10 , wherein the compound is selected from the group consisting of:

N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-(Benzoyloxy)propyl]-N,N-diethylcyclohexanaminium chloride;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethoxybenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-(2,4-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((3-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Fluoro-2-(trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-(Trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-nitrobenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3,5-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)-N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)-N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-(3-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]tetrahydro-2H-pyran-4-aminium iodide;

N-[2-((2,3-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((Cyclohexanecarbonyl)oxy)propyl]-N,N-diethylcyclohexanaminium iodide;

N-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-3-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((1-methyl-1H-pyrrole-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N- [2-((Benzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-methylthiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N,4-Trimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-DimethylbenzoyDoxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4,6-Trimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dimethylbenzoyl)oxy)propyl N,N-dimethylcyclohexanaminium iodide;

(S)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide; and

(R)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide.

Assignments (4)
CHANGE OF NAME Recorded Apr 6, 2023
From: ABS DEVELOPMENT 1, INC.
To: LIBERTAS BIO, INC.
Reel/Frame 063271/0055 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 20, 2022
From: ASANA BIOSCIENCES, LLC
To: ABS DEVELOPMENT 1, INC.
Reel/Frame 059968/0937 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 2, 2014
From: ENDO PHARMACEUTICALS INC.
To: ASANA BIOSCIENCES, LLC
Reel/Frame 033010/0256 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 9, 2014
From: THOMPSON, SCOTT KEVIN; SMITH, ROGER ASTBURY; GUPTA, SANDEEP; PRIESTLEY, TONY; LAPING, NICHOLAS JAMES; SAHA, ASHIS K.; RUDRA, SONALI
To: ENDO PHARMACEUTICALS INC.
Reel/Frame 032635/0195 →